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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61754Generated: October 25, 2026

1-Propanol → 6,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/reaction/61754

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-PropanolHCID 1031—
ReactantTriethylamineHCID 8471—
ReactantPotassium vinyltrifluoroborateHCID 23679353—
ReactantTrifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl esterHCID 86663817—
SolventWaterHCID 962—
Product6,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 6683405480%

Reaction Conditions

Temperature60 °C

Reaction Steps

Under nitrogen atmosphere, trifluoro-methanesulfonic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester (Compound B1, 1.00 g, 2.302 mmol) was added with n-propanol (20 mL), potassium vinyltrifluoroborate (854 mg, 3.0 eq.), dichloro-((bis-diphenylphosphino)ferrocenyl)palladium (217 mg, 0.1 eq.) and triethylamine (1.11 ml, 3.0 eq.) in order and the resultant was stirred at 60° C. for 4 hr. Upon the completion of the reaction, water was added to the reaction solution. The resulting precipitates were filtered and washed with distilled water, and the residues were dried to obtain the title compound (666 mg, 80%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440922B2
Source datasetuspto-grants-2016_09
ORD IDord-27637dfe19f8455bb26f5e4928000c58
Source noteuspto-grants-2016_09